Réaction #68746

Équation de réaction

2-bromo-3-methoxycyclopent-2-enone

4′-chloro-4-ethylbiphen-3-ylboronic acid

potassium phosphate

→

2-(4′-chloro-4-ethylbiphen-3-yl)-3-methoxycyclopent-2-enone

Rendement 75.5%

Conditions de réaction

Traitement

1. 1
   Autredegassed toluene (25 ml) under an atmosphere of nitrogen
2. 2
   Températureto cool to room temperature
3. 3
   Autrequenched with water (40 ml)
4. 4
   Extractionextracted with ethyl acetate (3×30 ml)
5. 5
   Lavagewashed with brine (15 ml)
6. 6
   Séchagedried over anhydrous magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   Autrethe filtrate is evaporated under reduced pressure
9. 9
   AutreThe residue is purified by column chromatography on silica gel

Mode opératoire

To a stirred suspension of 2-bromo-3-methoxycyclopent-2-enone (1.0 g, 5.23 mmol), 4′-chloro-4-ethylbiphen-3-ylboronic acid (2.03 g, 7.80 mmol) and potassium phosphate (2.23 g, 10.50 mmol) in anhydrous, degassed toluene (25 ml) under an atmosphere of nitrogen is added palladium(II)acetate (24 mg, 0.105 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (86 mg, 0.209 mmol). The reaction is heated at 90° C. for 4 hours and then allowed to cool to room temperature, quenched with water (40 ml) and extracted with ethyl acetate (3×30 ml). The organic extracts are combined, washed with brine (15 ml), dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure. The residue is purified by column chromatography on silica gel to give 2-(4′-chloro-4-ethylbiphen-3-yl)-3-methoxycyclopent-2-enone (1.29 g, 75%).

Source